3-Methyl-2-(methylsulfanyl)-5,5-diphenyl-3,5-dihydro-4H-imidazol-4-one

In the title molecule, C17H16N2OS, the dihydroimidazolone ring is slightly puckered and the methylsulfanyl group is nearly coplanar with it.


Structure description
Imidazole and its derivatives display various biological effects such as insecticides, herbicides and fungicides (Tutino et al., 2009;Wu et al., 2023;Takle et al., 2006). Our team has been working on these derivatives for some years to evaluate their biological activities (e.g. Guerrab et al., 2022a,b) and corrosion inhibition activities (e.g. Nabah et al., 2020). In a continuation of our recent work focused on the synthesis and biological evaluation of phenytoin derivatives (e.g. Guerrab et al., 2023), we report here the crystal structure of the title compound (Fig. 1).
The molecule adopts the conformation typical for this class of molecule with the phenyl groups projecting out above and below the plane of the dihydroimidazolone ring. The latter ring is slightly puckered [C1 and C2 deviate by À0.0122 (7) and 0.0121 (7) Å , respectively, from the mean plane] and the mean planes of the C4-C9 and C10-C15 rings are inclined to its mean plane by 72.32 (5) and 67.03 (3) , respectively. The terminal carbon atom of the methylsulfanyl group lies close to the mean plane of the dihydroimidazolone ring, as indicated by the C17-S1-C3-N2 torsion angle of À2.75 (13) . In the crystal, C7-H7Á Á ÁO1 hydrogen bonds (Table 1) form chains of molecules extending along the a-axis direction. These are linked by C15-H15Á Á ÁO1 hydrogen bonds, forming data reports corrugated layers of molecules parallel to the ac plane (Table 1 and Fig. 2). The layers pack along the b-axis direction with normal van de Waals contacts (Fig. 3) between them.

Synthesis and crystallization
Thiohydantoin (1000 mg, 3.73 mmol) was placed in a flask with K 2 CO 3 (1030 mg, 7.46 mmol) in 20 ml of absolute dimethylformamide (DMF), and two equivalents of iodomethane (0.5 ml, 1160 mg) were added. The solution was left stirring for 2 h at room temperature. The reaction mixture was filtered, and the solvent was distilled off under reduced pressure. The residue obtained was recrystallized from methanol solution to yield colorless, plate-like single crystals (Akrad et al., 2018).

Figure 2
A portion of one layer viewed along the b-axis direction with C-HÁ Á ÁO hydrogen bonds depicted by dashed lines. Non-interacting hydrogen atoms are omitted for clarity.

Figure 3
Packing viewed along the a-axis direction giving end views of parts of four layers with C-HÁ Á ÁO hydrogen bonds depicted by dashed lines. Noninteracting hydrogen atoms are omitted for clarity.

Special details
Experimental. The diffraction data were obtained from 15 sets of frames, each of width 0.5° in ω or φ, collected with scan parameters determined by the "strategy" routine in APEX4. The scan time was θ-dependent and ranged from 5 to 15 sec/frame.

data-2
IUCrData (2023). 8, x230208 Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. H-atoms attached to carbon were placed in calculated positions (C-H = 0.95 -0.98 Å). All were included as riding contributions with isotropic displacement parameters 1.2 -1.5 times those of the attached atoms.